Jake is a young boy, who lives in New York with his mom, dad, brother named Peter, and his sister named Maija. The time is 1937, so it is now the time of the Great Depression. Jake's family is in the middle of tough times, and they are not very wealthy. His parents go to lectures that tell about better living in different parts of the world. His mom and dad decide to move to Russia in the hopes of a better education and better jobs. When they get to the place, they set up a saw mill, but they get too few logs to saw, so they get less pay.

The Darkest Evening is about Jake's family which consists of his mother, father, and his brother, Peter who moved from Minnesota to Russia at the time that the Communists were taking people away and killing them just because they had the courage to speak against the Party. Jake's family moved to Russia to try to build a worker's paradise. Also, Russia has good schools that teach about Finnish culture. It didn't work out because the food was awful and they were scared of the Communists because everyone was getting taken unexpectedly.